1.
exo-Imino to endo-iminocyclitol rearrangement. A general route to five-membered antiviral azasugars.
Org Lett
; 8(16): 3465-7, 2006 Aug 03.
Artigo
em Inglês
| MEDLINE
| ID: mdl-16869636
RESUMO
A facile synthesis is reported for five-membered iminocyclitols which allows for variation in stereochemistry at all the chiral centers, diverse C1- and N-substitution, and the potential for a three-component combinatorial process. The key step is inversion at the C4 stereocenter (L-lyxo sugar --> D-ribono azasugar). The exo-imino to endo-iminocyclitol process was extended to the D-lyxo and the D- and L-hexose series. Some analogues were found to be more potent than N-butyl DNJ and N-nonyl DNJ in antiviral activity.